$51 Cheap flight deals from Orlando (ORL) to Deerfield (CHI)

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This Weekend's Flight Deals from Orlando to Deerfield

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jul 17 - Mon, Jul 20
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Jul 17 from Orlando Sanford Intl. to Greater Rockford, returning Mon, Jul 20, priced at $233 found 2 days ago
Fri, Jul 17 - Tue, Jul 21
MCO
Orlando Intl.
ORD
O'Hare Intl.
$304 Roundtrip, found 7 hours ago
$304
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Jul 17 from Orlando Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $304 found 7 hours ago
Sun, Jul 19 - Mon, Jul 20
MCO
Orlando Intl.
MDW
Midway Intl.
$400 Roundtrip, found 2 days ago
$400
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jul 19 from Orlando Intl. to Midway Intl., returning Mon, Jul 20, priced at $400 found 2 days ago

Airfares from $51 One Way, $90 Round Trip from Orlando to Deerfield

Prices starting at $90 for return flights and $51 for one-way flights to Deerfield were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Oct 5 - Wed, Oct 14
SFB
Orlando
RFD
Rockford
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Mon, Oct 5 from Orlando to Rockford, returning Wed, Oct 14, priced at $90 found 2 days ago
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando
ORD
Chicago
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Orlando to Chicago, returning Tue, Aug 25, priced at $98 found 3 days ago
Sat, Sep 5 - Sat, Sep 12
MCO
Orlando
ORD
Chicago
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Orlando to Chicago, returning Sat, Sep 12, priced at $102 found 4 days ago
Thu, Sep 24 - Mon, Sep 28
MCO
Orlando
MDW
Chicago
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 24 from Orlando to Chicago, returning Mon, Sep 28, priced at $189 found 1 day ago
Mon, Aug 10 - Mon, Aug 17
MCO
Orlando
MDW
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 10 from Orlando to Chicago, returning Mon, Aug 17, priced at $209 found 1 day ago

Deerfield economy flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9.2/10 Wonderful! (1,819 reviews)

Aug 14 - Aug 16

2 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $794, price is now $575 per person
$575
per person
found 1 day ago
Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking...

Reviewed on Jul 12, 2026

Kinzie Hotel
4.0-star property

Kinzie Hotel

9.2/10 Wonderful! (2,139 reviews)

Aug 30 - Sep 4

5 night stay

Orlando (MCO) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Orlando (MCO)

Frontier Airlines • Coach
Save 100% on your flight
Price was $983, price is now $704 per person
$704
per person
found 1 day ago
Great Staff. Super friendly and knowledgeable. Will be staying again. The beds are super comfortable.

Reviewed on Jul 9, 2026

Thompson Chicago, by Hyatt
4.5-star property

Thompson Chicago, by Hyatt

9.2/10 Wonderful! (1,388 reviews)

Sep 4 - Sep 7

3 night stay

Orlando (MCO) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $906, price is now $656 per person
$656
per person
found 1 day ago
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on Jul 12, 2026

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More About Flying To Deerfield from Orlando

Route Information for Flights from Orlando to Deerfield

Origin Airport IATA Code
ORL
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Orlando to Deerfield

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.